I used ChatGPT to celebrate International Joke Day — these 5 hilarious prompts had me crying with laughter

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If you ask me, the key to my eternal happiness is laughter.

Waking up every morning and pulling up a video of the latest “Donkey of the Day” induction into The Breakfast Club, revisiting a standup set from my new favorite comedian Henry Coleman or hopping on IG to watch another random skit elicits a few giggles from me before I enter my professional mode. It’s just impossible for me to enjoy the rest of the day unless I chuckle at something humorous first. And with a holiday like International Joke Day popping up on an annual basis, I get even more laughs since most folks get the memo to throw out their best material on my timeline.

My interactions with ChatGPT have been dedicated to prompts targeting self-discovery, productivity routines, decision-making, and more. International Joke Day gave me the bright idea to test the chatbot’s comedy expertise and see just how funny AI could be based on the prompts I feed it.

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While a standup routine written entirely by ChatGPT will probably get me thrown off the stage in mere seconds, the chatbot’s sense of humor proved to be surprisingly strong enough to make me unexpectedly laugh out loud a few times.

Getting the truest definitions of modern-day terms in the funniest way possible

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Words obviously have clear-cut meanings.

But when I talk about those words and other terms with my friends, they take on a more realistic definition based on the way they’re injected into our professional and personal lives. The terms “adulting”, “vacation” and “multitasking” are just a few of the words that adopt a whole new meaning when I apply a bit of honesty to them.

With the theme of brutal honesty in mind, I ran with this prompt to see how ChatGPT interprets modern-day terms: “Rewrite the dictionary with brutally honest definitions for modern life. Examples: Monday Zoom Meeting, Password, Printer, Group Project.” The chatbot proceeded to give me the truest definitions of a bunch of words, which turned out to be a lot funnier than expected and confirmed my exact opinions of each one:

  • Zoom Meeting: A gathering where everyone agrees it could have been an email.
  • Reply All: The fastest way to involve people who desperately wanted nothing to do with the conversation.
  • Wi-Fi: The invisible force holding modern civilization together.
  • Influencer: Someone who convinces thousands of people they discovered a product entirely by coincidence.
  • Update Available: An announcement that your device has chosen the least convenient moment to reinvent itself.
  • Weekend: Forty-eight hours dedicated to errands, chores, and wondering where the time went.
  • Smart Home: A house that's brilliant until the internet goes down.
  • Free Trial: A countdown to forgetting you've been charged.

Four other hilarious prompts that elicit plenty of laughter

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Instead of simply leading with “Tell me a joke” during another one of my daily ChatGPT convos, I came up with a few comedic prompts and even asked the chatbot to come up with a few that I could use to test its comedic side. The following four prompts did enough to convince me that ChatGPT is capable of being funny when it wants to:

  • The Roast Me Prompt: Roast me like you're a stand-up comedian doing crowd work. Keep it playful, original, and observant without being mean. Start gently, then gradually become more savage before ending with one surprisingly wholesome compliment.
  • The Honest Google Search Prompt: Rewrite common Google searches to reveal what people are actually thinking when they type them. Example: "How long does chicken last in the fridge?" → "Please tell me I don't have food poisoning."
  • The Passive Aggressive Superhero Prompt: Invent a superhero whose only power is passive aggression. Describe their origin story, powers, greatest enemy, and dramatic catchphrase.
  • The Fictional Villain Therapy Session Prompt: Imagine these famous villains are attending group therapy together [names of villains]. Write the conversation as they awkwardly try to explain why they're misunderstood while the therapist desperately keeps the session on track.

There’s definitely a lot of fun to be had when prompting ChatGPT to respond to prompts aimed at roasting, role-playing, creating absurd scenarios, interactive comedy and more.

Final thoughts

It turns out that prompting ChatGPT to act out a therapy session between The Joker, Darth Vader, Lord Voldemort and Thanos can produce tons of laughter from me and compel me to try that same experiment with other infamous bad guys & gals.

Finding the funny in everything is something I do (which some see as a character flaw, but whatever…), so it was pretty entertaining seeing how many funny ha-ha moments ChatGPT could produce with my prompts in mind.

Try one of them out for yourself to see just how brutal ChatGPT’s roast of your life can be (the more it learns about you, the more hilarious its revealing truths are).


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Elton Jones
AI Writer

Elton Jones covers AI for Tom’s Guide, and tests all the latest models, from ChatGPT to Gemini to Claude to see which tools perform best — and how they can improve everyday productivity.

He is also an experienced tech writer who has covered video games, mobile devices, headsets, and now artificial intelligence for over a decade. Since 2011, his work has appeared in publications including The Christian Post, Complex, TechRadar, Heavy, and ONE37pm, with a focus on clear, practical analysis.

Today, Elton focuses on making AI more accessible by breaking down complex topics into useful, easy-to-understand insights for a wide range of readers.

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